(1S,3'S)-5-methoxy-3'-(2-((S)-p-tolylsulfinyl)phenyl)-3,4-dihydro-2H-spiro[naphthalene-1,2'-oxirane] | 1029690-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,3'S)-5-methoxy-3'-(2-((S)-p-tolylsulfinyl)phenyl)-3,4-dihydro-2H-spiro[naphthalene-1,2'-oxirane]
• CAS: 1029690-24-1
• 化学式: C₂₅H₂₄O₃S
• 分子量: 404.53
• InChiKey: VVMSLVSDOYAXDR-QEMZJVQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,3'S)-5-methoxy-3'-(2-((S)-p-tolylsulfinyl)phenyl)-3,4-dihydro-2H-spiro[naphthalene-1,2'-oxirane] 以 氘代氯仿 为溶剂， 反应 1.0h， 以100%的产率得到(1R)-(5-methoxy-3,4-dihydronaphthalen-1-yl)-[(S)-2-(p-toluenesulfinyl)phenyl]methanol
  参考文献：
  名称：

  Stereoselective Alkylidenation of Ketones with 2-(p-Toluenesulfinyl)benzyl Iodide: Synthesis of Enantiomerically Pure Trisubstituted Epoxides

  摘要：

  de Alkylidenation of arylmethyl, dialkyl, and cyclic ketones with 2-(p-toluenesulfinyl)benzyl iodide in the presence of NaN(SiMe3)(2) takes place with a high or complete control of the facial selectivity at the carbonyl group (up to 98% de) and the carbanion (>98% de), respectively, yielding mixtures of only two optically pure trisubstituted epoxides (E/Z ratio ranges between 2:1 and >50:1). Removal of the P-tolylsulfinyl group with t-BuLi provides the corresponding (E)-3-phenyl-2,2-disubstituted epoxides without affecting their optical purity.

  DOI：

  10.1021/ol8005387
• 作为产物：
  描述：

  (S)-2-(p-toluenesulfinyl)benzyl iodide 、 5-甲氧基-3,4-二氢-2H-1-萘酮 在 sodium hexamethyldisilazane 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.02h， 以79%的产率得到(1S,3'S)-5-methoxy-3'-(2-((S)-p-tolylsulfinyl)phenyl)-3,4-dihydro-2H-spiro[naphthalene-1,2'-oxirane]
  参考文献：
  名称：

  Stereoselective Alkylidenation of Ketones with 2-(p-Toluenesulfinyl)benzyl Iodide: Synthesis of Enantiomerically Pure Trisubstituted Epoxides

  摘要：

  de Alkylidenation of arylmethyl, dialkyl, and cyclic ketones with 2-(p-toluenesulfinyl)benzyl iodide in the presence of NaN(SiMe3)(2) takes place with a high or complete control of the facial selectivity at the carbonyl group (up to 98% de) and the carbanion (>98% de), respectively, yielding mixtures of only two optically pure trisubstituted epoxides (E/Z ratio ranges between 2:1 and >50:1). Removal of the P-tolylsulfinyl group with t-BuLi provides the corresponding (E)-3-phenyl-2,2-disubstituted epoxides without affecting their optical purity.

  DOI：

  10.1021/ol8005387